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489-84-9 Usage

Chemical Properties

DARK BLUE LOW MELTING CRYSTALLINE SOLID

Originator

AZ 8,Millet Roux

Uses

Different sources of media describe the Uses of 489-84-9 differently. You can refer to the following data:
1. antioxidant, inhibits lipid peroxidation inhibitor, antiinflammatory, hepatoprotectant; LD50(rat) 1550 mg/kg po
2. Guaiazulene can be used as a starting material for the synthesis of:Azulene-based dye molecules such as 3-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanoacrylic acid and 5-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanopenta-2,4-dienoic acid.Stilbazulenyl nitrone, a second-generation azulenyl nitrone which can be used as a chain-breaking antioxidant.Bis-azulenyl based near-infrared fluorescence quencher.

Manufacturing Process

10 kg a gum of Guacum officinale was heated with 3-4 kg of sulfur to 130°C. The heating was slowly continued for 220°C under the nitrogen. The formed water steam was removed with the nitrogen current. The temperature should be higher 100°C in order to the water didnt fall into reaction mixture. H2S was obtained simultaneously the dehydrogenation and removed with water steam. Hydrogen sulfide was connected in an alkaline trap. When a H2S discharge stopped, the temperature was decreased to 120°C and the reaction mixture was distilled in vacuum 1-20 mm. The distillate had deep blue color and contained 6-7 kg oil with 20% of 7-isopropyl-1,4- dimethylazulene. It was dissolved in the 5-10 volumes of light petroleum, shook with sodium hydroxide for removing the sulfur containing substaneces, washed to neutral. Then petrolem layer was mixed with 10-15 L 62% H2SO4 for removing the by-products, the petroleum layer lost the blue color and the desired substance was in sulphuric acid layer. The last one was shook with ice and NaOH. As a result about 7% NaSO4 solution in sulfuric acid was obtained. It was diluted and azulene gave an emulsion, which was extracted with 10 L of petrolem and distilled. The 7-isopropyl-1,4-dimethylazulene is distilled at 167°-168°C/12 mm. Yield 10-15%.

Therapeutic Function

Antiinflammatory

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Purification Methods

It forms blue-violet plates from EtOH. Also redistil it in vacuo until distillate solidifies. UV has max at 284nm (log 4.6, heptane). The picrate has m 122o(EtOH). [Beilstein 5 III 1677, 5 IV 1751.]

Check Digit Verification of cas no

The CAS Registry Mumber 489-84-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 9 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 489-84:
(5*4)+(4*8)+(3*9)+(2*8)+(1*4)=99
99 % 10 = 9
So 489-84-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

489-84-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (G0228)  Guaiazulene  >99.0%(GC)

  • 489-84-9

  • 10g

  • 505.00CNY

  • Detail
  • Alfa Aesar

  • (A17690)  Guaiazulene, 98+%   

  • 489-84-9

  • 5g

  • 347.0CNY

  • Detail
  • Alfa Aesar

  • (A17690)  Guaiazulene, 98+%   

  • 489-84-9

  • 25g

  • 744.0CNY

  • Detail
  • Aldrich

  • (G11004)  Guaiazulene  99%

  • 489-84-9

  • G11004-10G

  • 459.11CNY

  • Detail
  • Aldrich

  • (G11004)  Guaiazulene  99%

  • 489-84-9

  • G11004-25G

  • 749.97CNY

  • Detail

489-84-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name guaiazulene

1.2 Other means of identification

Product number -
Other names Guaiazulene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:489-84-9 SDS

489-84-9Synthetic route

1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}-2-(3-guaiazulenyl)ethylene
1203707-11-2

1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}-2-(3-guaiazulenyl)ethylene

azulene
275-51-4

azulene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

2-(azulen-1-yl)-1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}ethylene
1314045-03-8

2-(azulen-1-yl)-1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}ethylene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;A 97%
B 58%
1-chloro-7-isopropyl-4-methyl-azulene
867380-19-6

1-chloro-7-isopropyl-4-methyl-azulene

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
With palladium diacetate; potassium phosphate In toluene at 100℃; for 24h;94%
azulene
275-51-4

azulene

1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene
741737-71-3

1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

1,3-bis[2,2-bis(4-methoxyphenyl)ethenyl]azulene
1314045-02-7

1,3-bis[2,2-bis(4-methoxyphenyl)ethenyl]azulene

C

2-(azulen-1-yl)-1,1-bis(4-methoxyphenyl)ethylene

2-(azulen-1-yl)-1,1-bis(4-methoxyphenyl)ethylene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;A 93%
B 19%
C 34%
1,1-bis[4-(dimethylamino)phenyl]-2-(3-guaiazulenyl)ethylene
1103995-55-6

1,1-bis[4-(dimethylamino)phenyl]-2-(3-guaiazulenyl)ethylene

azulene
275-51-4

azulene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

2-(azulen-1-yl)-1,1-bis[4-(dimethylamino)phenyl]ethylene
1314044-93-3

2-(azulen-1-yl)-1,1-bis[4-(dimethylamino)phenyl]ethylene

C

1,1-di(azulen-1-yl)-2,2-bis[4-(dimethylamino)phenyl]ethane
1314044-97-7

1,1-di(azulen-1-yl)-2,2-bis[4-(dimethylamino)phenyl]ethane

D

1,3-bis{2,2-bis[4-(dimethylamino)phenyl]ethenyl}azulene
1314044-96-6

1,3-bis{2,2-bis[4-(dimethylamino)phenyl]ethenyl}azulene

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; acetonitrile at 60℃; for 3h;A 91%
B 46%
C 13%
D 19%
dimethyl 3-isopropyl-6,11-dimethyltricyclo<6.2.2.01,7>dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate

dimethyl 3-isopropyl-6,11-dimethyltricyclo<6.2.2.01,7>dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate
98525-07-6, 72898-39-6, 98525-12-3, 98525-13-4

dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate

Conditions
ConditionsYield
In acetonitrile at 110℃; for 1h;A 29%
B 71%
In acetonitrile at 100℃; for 1h; in sealed tube;A 29%
B 71%
3-bromoguaiazulenium bromide

3-bromoguaiazulenium bromide

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

2,2'-biguaiazulenyl
17509-79-4

2,2'-biguaiazulenyl

Conditions
ConditionsYield
With methanol Title compound not separated from byproducts;A 50%
B 20%
ethanol
64-17-5

ethanol

bis(3,8-dimethyl-5-isopropyl-1-azulenyl) ketone
10487-58-8

bis(3,8-dimethyl-5-isopropyl-1-azulenyl) ketone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.166667h; Heating;
With toluene-4-sulfonic acid for 0.166667h; Mechanism; Heating; regioselectivity; other substrates;
ethanol
64-17-5

ethanol

Azulen-1-yl-(5-isopropyl-3,8-dimethyl-azulen-1-yl)-methanone
150985-85-6

Azulen-1-yl-(5-isopropyl-3,8-dimethyl-azulen-1-yl)-methanone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

ethyl azulene-1-carboxylate
1206-88-8

ethyl azulene-1-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 6h; Heating;
ethanol
64-17-5

ethanol

(5-Isopropyl-3,8-dimethyl-azulen-1-yl)-(4,6,8-trimethyl-azulen-1-yl)-methanone
150985-81-2

(5-Isopropyl-3,8-dimethyl-azulen-1-yl)-(4,6,8-trimethyl-azulen-1-yl)-methanone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

C

4,6,8-Trimethyl-azulene-1-carboxylic acid ethyl ester

4,6,8-Trimethyl-azulene-1-carboxylic acid ethyl ester

D

azulene
275-51-4

azulene

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.166667h; Heating;
ethanol
64-17-5

ethanol

1-[3-(5-Isopropyl-3,8-dimethyl-azulene-1-carbonyl)-4,6,8-trimethyl-azulen-1-yl]-ethanone
150985-82-3

1-[3-(5-Isopropyl-3,8-dimethyl-azulene-1-carbonyl)-4,6,8-trimethyl-azulen-1-yl]-ethanone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

1-acetyl-4,6,8-trimethylazulene
834-97-9

1-acetyl-4,6,8-trimethylazulene

C

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

D

3-Acetyl-4,6,8-trimethyl-azulene-1-carboxylic acid ethyl ester

3-Acetyl-4,6,8-trimethyl-azulene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 1h; Heating;
ethanol
64-17-5

ethanol

2,2,2-Trifluoro-1-[3-(5-isopropyl-3,8-dimethyl-azulene-1-carbonyl)-4,6,8-trimethyl-azulen-1-yl]-ethanone
150985-83-4

2,2,2-Trifluoro-1-[3-(5-isopropyl-3,8-dimethyl-azulene-1-carbonyl)-4,6,8-trimethyl-azulen-1-yl]-ethanone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate
81920-91-4

ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate

C

1-trifluoroacetyl-4,6,8-trimethylazulene
841-83-8

1-trifluoroacetyl-4,6,8-trimethylazulene

D

4,6,8-Trimethyl-3-(2,2,2-trifluoro-acetyl)-azulene-1-carboxylic acid ethyl ester

4,6,8-Trimethyl-3-(2,2,2-trifluoro-acetyl)-azulene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 2.5h; Heating; Further byproducts given;
guaia-1(5),6-diene
105369-35-5

guaia-1(5),6-diene

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
palladium on activated charcoal In xylene for 36h; Heating;
3-bromo-7-isopropyl-1,4-dimethylazulene
90052-61-2

3-bromo-7-isopropyl-1,4-dimethylazulene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

2,2'-biguaiazulenyl
17509-79-4

2,2'-biguaiazulenyl

C

7-(2-bromo-1-methylethyl)-1,4-dimethylazulene
90052-62-3, 123287-97-8

7-(2-bromo-1-methylethyl)-1,4-dimethylazulene

D

7-<(Z)-2-bromo-1-methylethenyl>-1,4-dimethylazulene
123279-26-5

7-<(Z)-2-bromo-1-methylethenyl>-1,4-dimethylazulene

E

7-<(E)-2-bromo-1-methylethenyl>-1,4-dimethylazulene
123257-39-6

7-<(E)-2-bromo-1-methylethenyl>-1,4-dimethylazulene

F

7-(1-bromomethyl-2-bromoethyl)-1,4-dimethylazulene
123257-26-1

7-(1-bromomethyl-2-bromoethyl)-1,4-dimethylazulene

Conditions
ConditionsYield
In benzene for 0.333333h; Product distribution; Ambient temperature; different solvent and reaction times;
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
With selenium at 300 - 350℃; for 0.833333h;
6-(3-guaiazulenyl)-1(6H)-guaiazulenone
111873-85-9, 119439-50-8

6-(3-guaiazulenyl)-1(6H)-guaiazulenone

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

5-isopropylidene-3,8-dimethyl-1(5H)-azulenone
111873-87-1

5-isopropylidene-3,8-dimethyl-1(5H)-azulenone

C

1-(3-guaiazulenyl)-6a-isopropyl-2,5-dimethyl-1,1a,3,6a-tetrahydrocyclopropainden-3-one
111873-84-8, 119479-40-2

1-(3-guaiazulenyl)-6a-isopropyl-2,5-dimethyl-1,1a,3,6a-tetrahydrocyclopropainden-3-one

Conditions
ConditionsYield
In octane at 80℃;
5-Isopropenyl-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulen-1-ol
144126-95-4

5-Isopropenyl-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulen-1-ol

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
With toluene-4-sulfonic acid 1) benzene, reflux, 2 h, 2) decaline, reflux, 2 h; Yield given. Multistep reaction;
alismol

alismol

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
palladium on activated charcoal at 320 - 330℃; for 0.0833333h; Heating;
5-(1-guaiazulenyl)-5,6-dihydro-9-isopropyl-1-methyl-4-nitrocyclopentaheptalene
151621-28-2

5-(1-guaiazulenyl)-5,6-dihydro-9-isopropyl-1-methyl-4-nitrocyclopentaheptalene

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

9-isopropyl-1-methyl-4-nitroaceheptylene

9-isopropyl-1-methyl-4-nitroaceheptylene

Conditions
ConditionsYield
With phosphoric acid
alismoxide

alismoxide

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
palladium on activated charcoal at 320 - 330℃; for 0.0833333h; Heating;
1-ethylideneguaiazulenium perchlorate

1-ethylideneguaiazulenium perchlorate

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Conditions
ConditionsYield
With 4,6,8-trimethylazulene In acetic acid for 2h; from boiling point to r.t.; Yield given;
dimethyl 3-isopropyl-6,11-dimethyltricyclo<6.2.2.01,7>dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate

dimethyl 3-isopropyl-6,11-dimethyltricyclo<6.2.2.01,7>dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate

A

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

B

dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate
98525-07-6, 72898-39-6, 98525-12-3, 98525-13-4

dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate

C

dimethyl (Z)-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethene-1,2-dicarboxylate
145948-89-6

dimethyl (Z)-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethene-1,2-dicarboxylate

Conditions
ConditionsYield
In decane at 60 - 80℃; Kinetics; Thermodynamic data; Mechanism; var. solv. and temp;
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

o-benzenedisulfonimide
4482-01-3

o-benzenedisulfonimide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(3-guaiazulenyl)(4-methoxyphenyl)methylium o-benzenedisulfonimide

(3-guaiazulenyl)(4-methoxyphenyl)methylium o-benzenedisulfonimide

Conditions
ConditionsYield
In acetonitrile at 20 - 25℃; for 2h;99%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

trichloroacetic acid anhydride
4124-31-6

trichloroacetic acid anhydride

3-trichloroacetylguaiazulene
846-33-3

3-trichloroacetylguaiazulene

Conditions
ConditionsYield
In dichloromethane98%
In dichloromethane76%
In dichloromethane
In dichloromethane at 20℃; for 2h;
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1,2-phenylenebis(3-guaiazulenylmethylium) bis(hexafluorophosphate)

1,2-phenylenebis(3-guaiazulenylmethylium) bis(hexafluorophosphate)

Conditions
ConditionsYield
In diethyl ether; acetonitrile at 25℃;98%
With hexafluorophosphoric acid In water; acetic acid at 25℃; for 2h;88%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

Glyoxal
131543-46-9

Glyoxal

α,α'-bis(3-guaiazulenylmethylium) bis(tetrafluoroborate)

α,α'-bis(3-guaiazulenylmethylium) bis(tetrafluoroborate)

Conditions
ConditionsYield
With tetrafluoroboric acid; acetic acid In water at 25℃; for 1h;98%
With tetrafluoroboric acid; acetic acid at 25℃; for 1h;98%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(3-guaiazulenyl)(2-thienyl)methylium hexafluorophosphate

(3-guaiazulenyl)(2-thienyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol at 25℃; for 0.5h;98%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

N-[(5-isopropyl-3,8-dimethylazulen-1-yl)methylene]-N-methylmethanaminium tetrafluoroborate

N-[(5-isopropyl-3,8-dimethylazulen-1-yl)methylene]-N-methylmethanaminium tetrafluoroborate

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.75h; Vilsmeier Reaction;
Stage #2: 7-isopropyl-1,4-dimethyl-azulene at 0 - 40℃; Vilsmeier Reaction;
Stage #3: With tetrafluoroboric acid In water
98%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene
741737-71-3

1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene

Conditions
ConditionsYield
With hydrogenchloride In methanol at 60℃; for 3h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

(3-guaiazulenyl)(4-hydroxyphenyl)methylium hexafluorophosphate

(3-guaiazulenyl)(4-hydroxyphenyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃; for 2h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(3-guaiazulenyl)(4-methoxyphenyl)methylium hexafluorophosphate

(3-guaiazulenyl)(4-methoxyphenyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃; for 2h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4'-methoxyazobenzene-4-carbaldehyde
3516-77-6

4'-methoxyazobenzene-4-carbaldehyde

(3-guaiazulenyl)[4-(4-methoxyphenylazo)phenyl]methylium hexafluorophosphate

(3-guaiazulenyl)[4-(4-methoxyphenylazo)phenyl]methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(E)-4-((4-methoxyphenyl)diazenyl)benzaldehyde
107321-41-5

(E)-4-((4-methoxyphenyl)diazenyl)benzaldehyde

C29H29N2O(1+)*F6P(1-)

C29H29N2O(1+)*F6P(1-)

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol at 25℃; for 2h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde
1609117-40-9

4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde

{4-[(E)-2-(3-guaiazulenyl)diazenyl]phenyl}(3-guaiazulenyl)methylium hexafluorophosphate

{4-[(E)-2-(3-guaiazulenyl)diazenyl]phenyl}(3-guaiazulenyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 20℃; for 2h;97%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

3-Bromoazulene-1,5-quinone
161126-12-1

3-Bromoazulene-1,5-quinone

5'-Isopropyl-3',8'-dimethyl-[1,1']biazulenyl-3,7-dione

5'-Isopropyl-3',8'-dimethyl-[1,1']biazulenyl-3,7-dione

Conditions
ConditionsYield
In methanol Ambient temperature;96%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

benzaldehyde
100-52-7

benzaldehyde

(3-guaiazulenyl)phenylmethylium hexafluorophosphate

(3-guaiazulenyl)phenylmethylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃; for 1.5h;96%
With hexafluorophosphoric acid In methanol at 25℃; for 1.5h;96%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

3-phenyl-propenal
104-55-2

3-phenyl-propenal

(2E)-1-(3-guaiazulenyl)-3-phenyl-2-propen-1-ylium hexafluorophosphate

(2E)-1-(3-guaiazulenyl)-3-phenyl-2-propen-1-ylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In diethyl ether; water; acetonitrile at 25℃; for 1h;96%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

(3-guaiazulenyl)(2-methoxyphenyl)methylium tetrafluoroborate

(3-guaiazulenyl)(2-methoxyphenyl)methylium tetrafluoroborate

Conditions
ConditionsYield
With tetrafluoroboric acid In methanol; water at 25℃; for 2h;96%
4-aminobenzaldehyde
556-18-3

4-aminobenzaldehyde

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde
1609117-40-9

4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde

Conditions
ConditionsYield
Stage #1: 4-aminobenzaldehyde With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 0.25h;
Stage #2: 7-isopropyl-1,4-dimethyl-azulene In ethanol; water at 20℃; for 2h;
96%
1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole
884866-01-7

1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(Z)-N-(2-(5-isopropyl-3,8-dimethylazulen-1-yl)-2-phenylvinyl)-4-methylbenzenesulfonamide

(Z)-N-(2-(5-isopropyl-3,8-dimethylazulen-1-yl)-2-phenylvinyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 60℃; for 2h; diastereoselective reaction;96%
With rhodium (II) octanoate dimer In 1,2-dichloro-ethane at 60℃; for 3h;96%
1-(4-methylbenzenesulfonyl)-4-(4-methylphenyl)-1,2,3-triazole

1-(4-methylbenzenesulfonyl)-4-(4-methylphenyl)-1,2,3-triazole

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(Z)-N-(2-(5-isopropyl-3,8-dimethylazulen-1-yl)-2-p-tolylvinyl)-4-methylbenzenesulfonamide

(Z)-N-(2-(5-isopropyl-3,8-dimethylazulen-1-yl)-2-p-tolylvinyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 60℃; for 3h; diastereoselective reaction;96%
With rhodium (II) octanoate dimer In 1,2-dichloro-ethane at 60℃; for 3h;96%
formaldehyd
50-00-0

formaldehyd

7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

3,3-methylenebis(guaiazulene)
55544-35-9

3,3-methylenebis(guaiazulene)

Conditions
ConditionsYield
With acetic acid at 25℃; for 1h;95%
With ethanol; sodium hydrogencarbonate
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

5-isopropyl-3,8-dimethylazulene-1-carbaldehyde
3331-47-3

5-isopropyl-3,8-dimethylazulene-1-carbaldehyde

Conditions
ConditionsYield
Stage #1: 7-isopropyl-1,4-dimethyl-azulene; N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 1h; Vilsmeier formylation;
Stage #2: With potassium hydroxide; water
95%
Stage #1: 7-isopropyl-1,4-dimethyl-azulene; N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 1h;
Stage #2: With water; potassium hydroxide
94%
With trichlorophosphate In benzene for 0.666667h;92%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

3-bromo-7-isopropyl-1,4-dimethylazulene
90052-61-2

3-bromo-7-isopropyl-1,4-dimethylazulene

Conditions
ConditionsYield
With N-Bromosuccinimide; hexamethylenetetramine In hexane95%
Multi-step reaction with 2 steps
1: Br2 / hexane / -20 °C
2: 100 percent / alkali
View Scheme
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

1-isopropyl-4-(3-guaiazulenylmethylium)benzene hexafluorophosphate

1-isopropyl-4-(3-guaiazulenylmethylium)benzene hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In acetic acid at 25℃; for 2h;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4-<<4'-(N,N-dimethylamino)phenyl-1'>azo>benzaldehyde
39208-00-9

4-<<4'-(N,N-dimethylamino)phenyl-1'>azo>benzaldehyde

{4-[4-(dimethylamino)phenylazo]phenyl}(3-guaiazulenyl)methylium hexafluorophosphate

{4-[4-(dimethylamino)phenylazo]phenyl}(3-guaiazulenyl)methylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol; water at 25℃;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

methyl 3,3,3-trifluoropyruvate
13089-11-7

methyl 3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(5-isopropyl-3,8-dimethylazulen-1-yl)propionic acid methyl ester
1198330-30-1

3,3,3-trifluoro-2-hydroxy-2-(5-isopropyl-3,8-dimethylazulen-1-yl)propionic acid methyl ester

Conditions
ConditionsYield
In hexane at 0℃; for 0.25h;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

(E)-4-((4-(dimethylamino)phenyl)diazenyl)benzaldehyde
39208-00-9

(E)-4-((4-(dimethylamino)phenyl)diazenyl)benzaldehyde

C30H32N3(1+)*F6P(1-)

C30H32N3(1+)*F6P(1-)

Conditions
ConditionsYield
With hexafluorophosphoric acid In methanol at 25℃; for 2h;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

ethyl 2-benzoyl-4-(4-methoxyphenyl)-4-oxobut-2-enoate
1316302-31-4

ethyl 2-benzoyl-4-(4-methoxyphenyl)-4-oxobut-2-enoate

ethyl 3-(guaiazulen-1-yl)-5-(4-methoxyphenyl)-2-phenylfuran-3-carboxylate
1447465-53-3

ethyl 3-(guaiazulen-1-yl)-5-(4-methoxyphenyl)-2-phenylfuran-3-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane for 5h; Reflux;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

4,4'-bis(dimethylamino)benzhydrol
119-58-4

4,4'-bis(dimethylamino)benzhydrol

bis(4-dimethylaminophenyl)(3-guaiazulenyl)methane
1562305-68-3

bis(4-dimethylaminophenyl)(3-guaiazulenyl)methane

Conditions
ConditionsYield
With o-benzenedisulfonimide In neat (no solvent) at 30℃; for 5.5h; Friedel-Crafts Alkylation;95%
7-isopropyl-1,4-dimethyl-azulene
489-84-9

7-isopropyl-1,4-dimethyl-azulene

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

2,2,2-trifluoro-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethanone
846-34-4

2,2,2-trifluoro-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethanone

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2.3h;94%
In dichloromethane

489-84-9Relevant articles and documents

ALISMOL AND ALISMOXIDE, SESQUITERPENOIDS OF ALISMA RHIZOMES

Oshima, Yoshiteru,Iwakawa, Tsuneo,Hikino, Hiroshi

, p. 183 - 186 (1983)

From the crude drug 'takusha', wich is the rhizomes of Alisma plantago-aquatica var. orientale, two new sesquiterpenoids, alismol and alismoxide, have been isolated.Their structures have been estabished on the basis of chemical and physical evidence to be 1β,5β-guaia-6,10(15)-dien-4-ol and 4,10-epoxy-1β,5β-guaia-6-ene, respectively. - Key Word Index: Alisma plantago-aquatica var. orientale; Alismataceae; sesquiterpenoid; guaiane skeleton; alismol; 1β,5β-guaia-6,10(15)-dien-4-ol; alismoxide; 4,10-epoxy-1β,5β-guaia-6-ene

Evstratova et al.

, (1967)

Plattner,Fuerst,Marti

, p. 2452,2460 (1949)

-

Ukita et al.

, p. 4584,4586 (1954)

-

Hoffmann,Siegel

, p. 533,535 (1975)

Rudloff,Nair

, p. 421,424 (1964)

Naves,Papazian,Perrottet

, p. 302,324 (1940)

Approach to the blues: A highly flexible route to the azulenes

Carret, Sebastien,Blanc, Aurelien,Coquerel, Yoann,Berthod, Mikael,Greene, Andrew E.,Depres, Jean-Pierre

, p. 5130 - 5133 (2007/10/03)

(Chemical Equation Presented) A palette of blues: Chlorobicyclo-[5.3.0] decatrienones are readily prepared from cycloheptatrienes by cycloaddition of dichloroketene, ring expansion with a diazoalkane, and dehydrochlorination in dimethylformamide. These compounds are used as intermediates in the regiocontrolled synthesis of a wide variety of natural and nonnatural azulenes (see scheme).

Reaction of Guaiazulene with Bromine in Hexane and in Aqueous Tetrahydrofuran

Nozoe, Tetsuo,Shindo, Kimio,Wakabayashi, Hidetsugu,Kurihara, Teruo,Uzawa, Jun

, p. 687 - 688 (2007/10/02)

2-Bromoguaiazulenium bromide and 3,3-dibromo guaiazulenium bromide were obtained respectively from the reaction of guaiazulene and its 3-bromo compound with 1 equivalent of bromine in hexane at -20 deg C.The former compound afforded in methanol a mixture of guaiazulene, 3,3'-biguaiazulene, and oligomers, and gave 3-bromoguiazulene quantitatively with alkali.Dibromoguiazulenium bromide afforded with further moles of bromine in aqueous THF a mixture of guaiazulenequinone, 3-bromo-1-hydroxyquaiazulen-5-one, and a dark blue solid A in different ratios depending on the reaction conditions.

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